Orchinol

Orchinol
Names

IUPAC name 5,7-dimethoxy-9,10-dihydrophenanthren-2-ol
Other names 9,10-Dihydro-5,7-dimethoxyphenanthren-2-ol
Identifiers
CAS Number	41060-20-2
ChemSpider	158032
Jmol interactive 3D	Image
PubChem	181686
InChI InChI=1S/C16H16O3/c1-18-13-8-11-4-3-10-7-12(17)5-6-14(10)16(11)15(9-13)19-2/h5-9,17H,3-4H2,1-2H3 Key: HOVUVTNDNLNINP-UHFFFAOYSA-N InChI=1/C16H16O3/c1-18-13-8-11-4-3-10-7-12(17)5-6-14(10)16(11)15(9-13)19-2/h5-9,17H,3-4H2,1-2H3 Key: HOVUVTNDNLNINP-UHFFFAOYAM
SMILES COC1=CC(=C2C(=C1)CCC3=C2C=CC(=C3)O)OC
Properties
Chemical formula	C₁₆H₁₆O₃
Molar mass	256.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Orchinol is a 9,10-dihydrophenanthrene, a type of phenanthrenoid. It can be isolated from infected Orchis militaris and infected Loroglossum hircinum^[1] with Rhizoctonia repens.^[2] This molecule has a phytoalexin effect. It reduces the growth of Cattleya aurantiaca seedlings^[3] and has an antifungal activity.^[4]

References

↑ Structure of Orchinol, Loroglossol, and Hircinol. Roy M. Letcher and Llewellyn R. M. Nhamo, J. Chem. Soc., Perkin Trans. 1, 1973, pages 1263-1265, doi:10.1039/P19730001263
↑ Orchinol. Richard Braun, Moderne Methoden der Pflanzenanalyse, 1963, Volume 6, pages 130-134, doi:10.1007/978-3-642-94878-7_7 (article in German)
↑ Effects of Orchinol, Loroglossol, Dehydroorchinol, Batatasin III, and 3,4'- Dihydroxy-5-Methoxydihydrostilbene on Orchid Seedlings. Katherine A. Hills, Albert Stoessl, Allison P. Oliva and Joseph Arditti, Botanical Gazette, September 1984, Vol. 145, No. 3, pages 298-301 (link)
↑ Structure and antifungal activity of hircinol, loroglossol and orchinol. M.H. Fisch, Brigitta H. Flick and J. Arditti, Phytochemistry, February 1973, Volume 12, Issue 2, Pages 437–441, doi:10.1016/0031-9422(73)80036-6

External links

Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)

Phenanthrols

1-Phenanthrol
2-Phenanthrol
3-Phenanthrol
4-Phenanthrol
9-Phenanthrol

polyhydroxylated phenanthrenes

coeloginanthrin (3,5,7-trihydroxy-1,2-dimethoxyphenanthrene)
confusaridin (2,6-dihydroxy-3,4,7,8-tetramethoxyphenanthrene)
confusarin (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene)
dehydroeffusol
dehydrojuncusol (1,6-dimethyl-5-vinyl-8-phenanthrene-2,7-diol)
flavanthrinin (2,7-dihydroxy-4-methoxyphenanthrene)
gymnopusin (2,7-dihydroxy-3,4,9-trimethoxyphenanthrene)
Nudol (2,7-dihydroxy-3,4-dimethoxyphenanthrene)
Perakensol (7-hydroxy-2,3,6-trimethoxyphenanthrene)
plicatol A (2,5-dihydroxy-4,9,10-trimethoxyphenanthrene)
Plicatol B (2,5-dihydroxy-4-methoxyphenanthrene)

2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene
2,5-dihydroxy-3,4-dimethoxyphenanthrene
2,5-dihydroxy-3,4,9-trimethoxyphenanthrene
2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
2,7-dihydroxy-3,4,9-trimethoxyphenanthrene
2,7-Dihydroxy-3,6-dimethoxyphenanthrene
3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene
2-hydroxy-3,5,7-trimethoxyphenanthrene
2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene
3,4,8-Trimethoxyphenanthrene-2,5-diol
4,6-dimethoxyphenanthrene-2,3,7-triol
4,9-dimethoxyphenanthrene-2,5-diol
7-Hydroxy-2,3,4,8-tetramethoxyphenanthrene

9,10-dihydrophenanthrene derivatives

coelogin (2,6-Dihydroxy-7,8-dimethoxy-9,10-dihydro-5H-phenanthro[4,5-bcd]pyran)
coeloginin (2,6-Dihydroxy-7,8-dimethoxy-9,1O-dihydro-5H-phenanthro[4,5-bcd]pyran-5-one)
coeloginanthridin (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene)
coelonin (9,10-dihydro-2,7-dihydroxy-4-methoxyphenanthrene)
effusol (5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol)
hircinol (9,10-dihydro-4-methoxyphenanthrene-2,5-diol)
juncusol (1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol)
loroglossol (5-hydroxy-2,4-dimethyoxy-9,10-dihydrophenanthrene)
orchinol (9,10-Dihydro-5,7-dimethoxyphenanthren-2-ol)
Plicatol C (2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene)
4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol
4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol
9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene
9,10-dihydro-2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol
9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene

glycosides

Phenanthrene glycosides	denneanoside A, B, C, D and E

9,10-dihydrophenanthrene glycoside	denneanoside F

dimeric phenanthrenes

cirrhopetalanthrin (2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl)
flavanthrin (9,9′,10,10′-tetrahydro-2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl)
reptanthrin
isoreptanthrin
8,8'-bidehydrojuncusol (1,1',6,6'-tetramethyl-5,5'-divinyl-8,8'-biphenanthrene-2,2',7,7'-tetraol)

Cyclic bibenzyl-dihydrophenanthrene derivative

Cavicularin

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